Thiophenesulfonylurea derivatives and herbicidal composition containing the same

ABSTRACT

The present invention relates to a thiophenesulfonylurea derivative represented by general formula (I), the process for preparation thereof, and herbicide using it; and a salt thereof, in which T represents a group T1, T2, or T3 having general formulae (a), wherein E represents a direct bond; R represents hydrogen or C 1-4  acyl; R 1  represents C 1-6  alkyl substituted with 1 to 3 halogen atoms; R 2  represents hydrogen, C 1-3  alkyl, C 1-3  haloalkyl, halogen, cyano, C 1-3  alkoxy, C 1-3  haloalkoxy, amino, methylamino, dimethylamino, or C 1-3  alkyl substituted with C 1-2  alkoxy, C 1-2  haloalkoxy, thiol, methylthio, cyano or hydroxy; A represents a group selected from A1 to A4 having general formulae (b), and a herbicidal composition containing these derivatives.

This application is a 371 of PCT/KR94/00161 filed on Nov. 9, 1994.

This application is a 371 of PCT/KR94/00161 filed on Nov. 9, 1994.

TECHNICAL FIELD

The present invention relates to a novel thiophenesulfonylureaderivative represented by the following general formula (I): ##STR1##and a salt thereof, in which T represents a group T1, T2, or T3 havingthe following general formula: ##STR2## wherein E represents a directbond;

R represents hydrogen or C₁₋₄ acyl;

R¹ represents C₁₋₆ alkyl substituted with 1 to 3 halogen atoms;

R² represents hydrogen, C₁₋₃ alkyl, C₁₋₃ haloalkyl, halogen, cyano, C₁₋₃alkoxy, C₁₋₃ haloalkoxy, amino methylamino, dimethylamino, or C₁₋₂ alkylsubstituted with C₁₋₂ alkoxy, C₁₋₂ haloalkoxy, thiol, methylthio, cyanoor hydroxy;

A represents a group selected from A1 to A4 having the following generalformulae: ##STR3## wherein X represents hydrogen, C₁₋₄ alkyl, C₁₋₄alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, C₁₋₄ alkylthio, C₁₋₄haloalkylthio, halogen, C₂₋₅ alkoxyalkyl, C₂₋₅ alkoxyalkoxy, imino, C₁₋₃alkylamino, di(C₁₋₃ alkyl) amino or C₃₋₅ cycloalkyl;

X¹ represents C₁₋₂ alkyl, C₁₋₂ alkoxy or C₁₋₂ alkylthio;

Y represents hydrogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₁₋₄haloalkylthio, C₁₋₄ alkylthio, C₂₋₅ alkoxyalkyl, C₂₋₅ alkoxyalkoxy,amino, C₁₋₃ alkylamino, di(C₁₋₃ alkyl)amino, C₃₋₄ alkenyloxy, C₃₋₄alkynyloxy, C₂₋₅ alkylthioalkyl, C₁₋₄ haloalkyl, C₂₋₄ alkynyl, azido,cyano, C₂₋₅ alkylsulfinylalkyl, C₂₋₅ alkylsulfonylalkyl, hydroxymethyl,C₃₋₅ cycloalkyl or C₃₋₅ cloalkoxy;

Y¹ represents oxygen or methylene;

Y² represents hydrogen or methyl; and

Z represents N or CH; provided that

(1) when X is fluoro, chloro/iodo, Z represents CH and Y representsmethoxy, ethoxy, methoxymethyla-mino, amino, methylamino, dimethylaminoor difluoromethoxy and

(2) when X or Y is difluoromethoxy, Z represents CH and

(3) when the total number of carbon atoms of X and Y is 4 or more, R²represents a group having up to 4 carbon atoms.

The present invention also relates to a process for preparation of thecompound of formula (I), as defined above, and a herbicidal compositioncontaining the compound (I) as an active ingredient.

BACKGROUND ART

In the prior art, numerous sulfonylurea derivatives have been well knownas having herbicidal activity. For example, Korean Patent ApplicationNo. 91-3704 discloses a compound represented by the following generalformula(A): ##STR4## in which R¹¹ represents C₁₋₆ alkyl substituted with1 to 3 halogen atoms;

R¹² represents hydrogen, halogen, substituted alkyl group, substitutedalkoxy group, etc.;

R¹³ represents hydrogen or methyl;

A represents a pyrimidine or triazine derivative.

In addition, Korean Patent Application No. 91-4063 discloses a compoundrepresented by the following general formula (B): ##STR5## in which Prepresents a group P1, P2 or P3 having the following general formula:##STR6## wherein E represents CH₂ or a direct bond;

R¹⁴ represents ##STR7## wherein, R16 represents C₁₋₆ alkyl substitutedwith 1 to 3 halogen atoms,

R¹⁷ and R¹⁸ each independently represents C₁₋₄ alkyl,

R¹⁹ and R²⁰ each independently represents hydrogen, C₁₋₃ alkyl, or C₁₋₃haloalkyl, and

a represents O or S;

R¹⁵ represents hydrogen, halogen, substituted alkyl, etc.;

A represents a pyrimidine or triazine derivative.

However, those prior herbicidal sulfonylurea derivatives are undesirabledue to their poor herbicidal activity and selectivity on undesirableweeds to be controlled.

Thus, the present inventors have extensively studied to develope anexcellent herbicidal compound having herbicidal activity and selectivityon undesirable weeds to be controlled. As a result, we found that thecompound of formula (I), as defined above, according to the presentinvention provide the desired potent herbicidal activity and selectivityand thus completed the present invention.

DISCLOSURE OF INVENTION

Accordingly, it is an object of the present invention to provide a novelthiophenesulfonylurea derivative represented by the following generalformula (I): ##STR8## and a salt thereof, in which T represents a groupT1, T2or T3 having the following general formula: ##STR9## wherein Erepresents a direct bond;

R represents hydrogen or C₁₋₄ acyl;

R¹ represents C₁₋₆ alkyl substituted with 1 to 3 halogen atoms;

R² represents hydrogen, C₁₋₃ alkyl, C₁₋₃ haloalkyl, halogen, cyano, C₁₋₃alkoxy, C₁₋₃ haloalkoxy, amino, methylamino, dimethylamino, or C₁₋₂alkyl substituted with C₁₋₂ alkoxy, C₁₋₂ haloalkoxy, thiol, methylthio,cyano or hydroxy;

A represents a group selected from A1 to A4 having the following generalformulae: ##STR10## wherein X represents hydrogen, C₁₋₄ alkyl, C₁₋₄alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, C₁₋₄ alkylthio, C₁₋₄haloalkylthio, halogen, C₂₋₅ alkoxyalkyl, C₂₋₅ alkoxyalkoxy, imino, C₁₋₃alkylamino, di(C₁₋₃ alkyl)amino or C₃₋₅

X¹ represents C₁₋₂ alkyl, C₁₋₂ alkoxy or

C₁₋₂ alkylthio;

Y represents hydrogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₁₋₄haloakylthio, C₁₋₄ alkylthio, C₂₋₅ alkoxyalkyl, C₂₋₅ alkoxyalkoxy,amino, C₁₋₃ alkylamino, di(C₁₋₃ alkyl)amino, C₃₋₄ alkenyloxy, C₃₋₄alkynyloxy, C₂₋₅ alkylthioalkyl, C₁₋₄ haloalkyl, C₂₋₄ alkynyl, azido,cyano, C₂₋₅ alkylsulfinylalkyl, C₂₋₅ alkylsulfonylalkyl, hydroxymethyl,C₃₋₅ cycloakyl or C₃₋₅ cycloalkoxy;

Y¹ represents oxygen or methylene;

Y² represents hydrogen or methyl; and

Z represents N or CH;

provided that (1) when X is fluoro, chloro, iodo, Z represents CH and Yrepresents methoxy, ethoxy, met-hoxymethylamino, amino, methylamino,dimethylamino or difluoromethoxy and

(2) when X or Y is difluoromethoxy, Z represents CH and

(3) when the total number of carbon atoms of X and Y is 4 or more, R²represents a group having up to 4 carbon atoms.

It is another object of the present invention to provide a process forpreparing the compound of formula (I) and a salt thereof as definedabove, characterized in that

(a) in order to prepare a compound of formula (I) wherein R is acyl,i.e. a compound of the following general formula (I-4), (i-5), or (I-6):##STR11## wherein R¹, R² and A are defined as previously described, and

P represents a protecting group which can be easily removed by an acidor an alkali hydrolysis or by any other method, preferably C₁₋₄ acyl andmost preferably acetyl,

a compound having the following general formula (II) corresponding tothe desired product, i.e. a compound of formula (II-1), (II-2) or(II-3): ##STR12## wherein R¹ R² and P are defined as previouslydescribed, is reacted with a compound of the following general formula(III): ##STR13## wherein A is defined as previously described, in anappropriate reaction-inert solvent in the presence of a base, or

(b) in order to prepare a compound of formula (I) wherein R is hydrogen,i.e. a compound of the following general formula (I-1), (I-2), or (1-3):##STR14## wherein R¹, R² and A are defined as previously described, acompound having the general formula (I-4), (I-5) or (I-6), respectively,obtained in (a) is hydrolyzed with an alkali in the presence of water oran organic solvent.

It is a further object of the present invention to provide an herbicidalcomposition containing a novel thiophenesulfonylurea derivative asdefined above.

BEST MODE FOR CARRYING OUT THE INVENTION

In one aspect, the present invention relates to a novelthiophenesulfonylurea derivative represented by the following generalformula (I): ##STR15## and a salt thereof, in which T and A are asdefined above.

In the foregoing definitions for the substituents of the compound offormula (I) according to the present invention, the term "alkyl" definesstraight or branched saturated hydrocarbon radicals such as methyl,ethyl, n-propyl, isopropyl or butyl isomers when it is used alone or inthe composite form such as "alkylthio" or "haloalkyl"; the term "alkoxy"defines a straight or branched lower alkoxy group having 1 to 6 carbonatoms such as methoxy, ethoxy, n-propoxy, isopropoxy or butoxy isomers;the term "alkenyl" defines a straight or branched alkenyl group having 2to 7 carbon atoms and a double bond such as vinyl, 1-propenyl,2-propenyl, or isomers of butenyl, pentenyl, hexenyl or heptenyl; theterm "alkynyl" defines a straight or branched alkynyl group having 2 to7 carbon atoms and a triple bond such as ethynyl, 1-propynyl,2-propynyl, or isomers of butynyl, pentynyl or hexynyl; and the term"halogen" or "halo" in composite form defines fluorine, chlorine,bromine or iodine.

The preferred herbicidal compounds of formula (I) are those wherein Trepresents T1, T2 or T3 wherein R represents hydrogen or acetyl, R¹represents methyl or ethyl substituted with halogen and R² representshydrogen; and A represents A1 wherein X and Y each independentlyrepresents C₁₋₄ alkyl, C₁₋₄ alkoxy or halogen and Z represents N or CH.

More preferred compounds of formula (I) are those wherein T representsT1 wherein R represents hydrogen or acetyl, R¹ represents methyl orethyl substituted with fluorine or chlorine and R² represents hydrogen;and A represents A1 wherein X and Y each independently representsmethyl, methoxy or chloro and Z represents N or CH.

The most preferred compounds of formula (I) are those wherein Trepresents T1 wherein R represents hydrogen, R¹ represents 1-fluoroethyland R² represents hydrogen or chloroethyl; and A represents A1 wherein Xand Y each represents methoxy and Z represents CH.

In another aspect, the present invention relates to a process forpreparing the compound of formula (I) as defined above.

According to the present invention, the compound of formula (I) whereinR is hydrogen can be prepared by hydrolysing a compound of generalformula (I-4), (I-5) or (I-6) with a base in the presence of water or anorganic solvent to produce a compound of formula (I-1), (I-2) and (I-3),respectively, as depicted in the following reaction scheme: ##STR16## Inthe above reaction scheme,

represents a protecting group which can be easily removed by an acid oran alkali hydrolysis or by any other method, preferably C₁₋₄ acyl andmost preferably acetyl.

Hydrolysis of the compounds of formulae (I-4) to (I-6) can be conductedby removing a protecting group with a suitable alkali. Suitable alkaliwhich can be preferably used for this purpose includes sodium hydroxide,potassium hydroxide, lithium hydroxide, sodium carbonate, potassiumcarbonate and the like, with lithium hydroxide being most preferable.

Hydrolysis reaction can be conducted optionally in a reaction-inertsolvent, for example, water or organic solvent such as methanol,ethanol, tetrahydrofuran(THF), etc., or the mixture of water and suchorganic solvent, at the reaction temperature of 0 to 90° C., preferably0° to 30° C., for 1 to 24 hours, preferably 2 to 4 hours.

The resulting compound of formula (I) wherein R is hydrogen can beeasily separated by acidifying with aqueous hydrochloric acid solution.Specifically, the resulting compound can be conveniently obtained byacidifying the reaction mixture with aqueous hydrochloric acid solution,extracting the product with a solvent such as MC(methylene chloride),EA(ethyl acetate), etc. and then concentrating the extract tocrystallize the desired product. In addition, when it is desired toobtain the compound of formula (I) wherein R is hydrogen in a highlypurified form, the resulting product can be further purified with columnchromatography on silica gel.

The compounds of formulae (I-4) to (I-6) used as starting substances inthe above reaction scheme 1 can be prepared by reacting a novel compoundof the following general formula (II) corresponding to the desiredproduct, i.e. a compound of formula (II-1), (II-2) or (II-3), with acompound of the following general formula (III): ##STR17## Wherein R¹and R² in formulae (II-1) to (II-3) and A in formula (III) are definedas previously described.

The above reaction for elimination of a phenol group can be carried outin an appropriate reaction-inert solvent, for example, an aliphatic oraromatic organic solvent such as dioxane, acetonitrile, THF, acetone,methylene chloride, toluene, butanone, etc. In this reaction, a smallquantity of a strong base e.g. Dabco(1,4-diazabicyclo 2,2,2!octane),DHU(1,8-diazabicyclo 5,4,0!undece-7-ene), etc. can also be used as areaction auxilliary and the reaction temperature is maintainedpreferably at the range of 20° to 80° C. Alternatively, this reactioncan be conducted using an acid as described in U.S. Pat. No. 4,443,245.

The carbamate (III) used in the above reaction can be prepared byreacting diphenylcarbonate or phenylchloroformate with a correspondingamine in the presence of a base like pyridine, according to thefollowing reaction scheme: ##STR18## The novel compound of formula (II)including compounds of formulae (II-1), (II-2) and (II-3), can besynthesized according to the following reaction scheme: ##STR19##

The above reaction will be specifically explained hereinafter. First, at-butylsulfonamide of formula (V) is treated with 2 equivalences ofn-butyllithium in the presence of THF, 1,2-dimethoxyethane or ether,preferably in THF, at -90° to -50° C. for 1 to 24 hours to produce adili-thio salt to which a compound of formula ##STR20##

(where in L represents alkoxy, dimethylamide or methyl(methoxy)amide andthe like) while maintaining the temperature of -80° to -70° C. toproduce a ketone compound. The resulting ketone compound is treated witha reductant like sodium borohydride to produce a hydroxy compound. Sucha direct lithiation method of arylsulfonamide can easily be conducted byreferring J. G. Lombardino, J. Org. Chem., 36, 1843 (1971) and Stowell,J. G., "Carbanions in Org. Synthesis", John Wiley & Sone New York, 1979,Snieckus, V. Tetrahedron Lett. 26, 1145 (1985) and ibid. 1149 (1985)).In addition, the acylation reaction of a lithiated carbanion and thereduction of ketone compound with lithium aluminumhydride or sodiumborohydride to hydroxy compound have been well known in this art.

Then, the hydroxy compound thus produced above is O-acylated with aceticanhydride in the presence of pyridine to obtain a sulfonamide compound.This O-acylation reaction can be facilitated by adding DMAP(4-dimethylaminopyridine) as a catalyst. Finally, the resultingsulfonamide compound is stirred together with an excessive amount oftrifluoroacetic acid (about 0.3M) at 0° to 50° C. for 1 to 72 hours toremove N-t-butyl group and to obtain the desired primary sulfonamidecompound of formula (II).

This reaction can easily be practiced by a person having ordinaryknowledge of organic synthesis by referring J. D. Cart and W. L. Matier,J. Org. Chem., 39, 566 (1974) or by referring J. G. Lombardino, J. Org.Chem., 36, 1843 (1971) when treating with polyphosphoric acid.

The resulting product can be separated by evaporating any volatilesubstance in the reaction mixture under vacuum and crystallizing theresidue with an appropriate solvent such as diethylether, EA, etc. Inthis case, R¹ represents a substituent which is stable against a highlyreactive reagent such as n-BuLi.

On the other hand, a heterocyclic amine compound of formula (IV) abovecan be easily prepared by known processes disclosed in literature orsimply modified processes thereof. For example, a method for preparationof amino pyrimidine and triazine substituted with acetal is described inEuropean Patent Application No. 84,224 (published on Jul. 27, 1983) anda report, W. Braker, J. Am. Chem. Soc., 69, 3072 (1947); a method forpreparation of amino pyrimidine and triazine substituted with haloalkoxyor haloalkylthio such as OCHF₂, SCHF₂, OCH₂ OCH₂ CF₃, etc. is disclosedin European Patent No. 72,347 and U.S. Pat. Nos. 4,443,243 and4,487,915; and a method for preparetion of cyclopropyl pyrimidine andtriazine compounds substituted with alkyl, haloalkyl, alkoxy,haloalkoxy, alkylamino, dialkylamino or alkoxyalkyl, etc. is disclosedin European Patent No. 108,708 and U.S. Pat. Nos. 4,515,626 and4,600,428. In addition, the method for preparation of 5,6-dihydrofuro2,3-d!pyrimidine-2-amine cyclopenta d!pyrimidine-2-amine which arecompounds of formula (IV) wherein A is A2, and 6,7-dihydro-5H-pyrano2,3-d!pyrimidine-2-amine which is the compound of for wherein A is A3 isdisclosed in European Patent Application No. 15,863; and the method forpreparation of 2,3-d!pyrimidine -2-amine compound which is the compoundof formula (IV) wherein A is A4 is disclosed in European PatentApplication No. 46,677. Further, general methods for preparing aminopyrimidine compounds are fully described in several references (e.g."The Chemistry of Heterocyclic Compounds", Series. IntersciencePublishers, Inc., New York and London; "Pyrimidines", Vol. 16, D. J.Brown Ed; "S-Triazines and Derivatives", Vol. 13, E. M. Smolin and L.Rapaport) and the methods for preparing triazine compounds are alsodescribed in another references (e.g. F. C. Schaefer, U.S. Pat. No.3,154,547 and K. R. Huffman and F. C. Schaefer, J. Org. Chem., 28. 1812(1963)).

An appropriate salt of the compound of formula (I) prepared according tothe present invention above is also useful as a herbicide. Such saltform of the compound (I) can be conveniently prepared by various methodsconventionally used in this art. Specifically, the salt form of thecompound (I) can be conveniently obtained by treating an acid form ofthe compound (I) with a sutable base, for example, a solution of alkalimetal or alkaline earth metal salt having a strong basic anion such ashydroxide, alkoxide, or carbonate. In addition, a quarternary amine saltof the compound (I) can be prepared by means of an analogous method.

The salt of the compound of formula (I) can also be obtained byexchaning a cation with another one. Generally, this cation exchangereaction can be conducted by contacting an aqueous salt solution of thecompound (I) such as aqueous alkali metal salt solution or aqueousquarternary amine salt solution directly with a solution containing anyother cation to be exchanged. This exchange reaction can be mostefficiently carried out when the salt resulting from the cation exchangereaction is insoluble in water and therefore can be easily separated byfiltration.

Alternatively, such ion exchange reaction can be also carried out bysubjecting the aqueous solution of the salt of compound (I) to a columnfilled with a cation exchange resin containing a desired cation to beexchanged. In this method, the desired product is eluted from the columnwhile the original cation of the salt is exchanged with the cation ofresin. This method is particularly available when the desired salt iswater soluble, that is, it is sodium, potassium, or calcium salt.

Typical examples of the novel compound represented by the generalformula (I) which can be prepared according to the process of thepresent invention are listed in the following Tables 1, 2, and 3.

                                      TABLE 1                                     __________________________________________________________________________     ##STR21##                                                                    Comp.                                                                         No. R    R.sup.1                                                                             X    Y    Z m.p. (°C.)                                                                  Remarks                                       __________________________________________________________________________         ##STR22##                                                                         FCH.sub.2                                                                           CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              131-134                                            2                                                                                  ##STR23##                                                                         FCH.sub.2                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              158-160                                            3                                                                                  ##STR24##                                                                         FCH.sub.2                                                                           CH.sub.3                                                                           CH.sub.3 O                                                                         N 154-156                                            4   H    FCH.sub.2                                                                           CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              135-136                                            5   H    FCH.sub.2                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              128-129                                            6   H    FCH.sub.2                                                                           CH.sub.3                                                                           CH.sub.3 O                                                                         N 98-100                                             7                                                                                  ##STR25##                                                                         ClCH.sub.2                                                                          CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              150-151                                            8                                                                                  ##STR26##                                                                         ClCH.sub.2                                                                          CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              182-184                                            9                                                                                  ##STR27##                                                                         ClCH.sub.2                                                                          CH.sub.3                                                                           CH.sub.3 O                                                                         N 161-162                                            10                                                                                 ##STR28##                                                                         ClCH.sub.2                                                                          CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              182-184                                            11  H    ClCH.sub.2                                                                          CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              146-148                                            12  H    ClCH.sub.2                                                                          CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              141-142                                            13  H    ClCH.sub.2                                                                          CH.sub.3                                                                           CH.sub.3 O                                                                         N 158-159                                            14  H    ClCH.sub.2                                                                          CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              143-144                                            15                                                                                 ##STR29##                                                                         CH.sub.3 CHCl                                                                       CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              162-164                                                                            mixture                                       16                                                                                 ##STR30##                                                                         CH.sub.3 CHCl                                                                       CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              167-168                                                                            polar                                         17                                                                                 ##STR31##                                                                         CH.sub.3 CHCl                                                                       CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              170-172                                                                            nonpolar                                      18                                                                                 ##STR32##                                                                         CH.sub.3 CHCl                                                                       Cl   CH.sub.3 O                                                                         CH                                                                              169-170                                                                            mixture                                       19                                                                                 ##STR33##                                                                         CH.sub.3 CHCl                                                                       Cl   CH.sub.3 O                                                                         CH                                                                              172-174                                                                            polar                                         20                                                                                 ##STR34##                                                                         CH.sub.3 CHCl                                                                       Cl   CH.sub.3 O                                                                         CH                                                                              177-178                                                                            nonpolar                                      21                                                                                 ##STR35##                                                                         CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              176-178                                                                            mixture                                       22                                                                                 ##STR36##                                                                         CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              182-183                                                                            polar                                         23                                                                                 ##STR37##                                                                         CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              185-186                                                                            nonpolar                                      24                                                                                 ##STR38##                                                                         CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3 O                                                                         N 156-157                                                                            mixture                                       25                                                                                 ##STR39##                                                                         CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3 O                                                                         N 163-164                                                                            polar                                         26                                                                                 ##STR40##                                                                         CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3 O                                                                         N 167-168                                                                            nonpolar                                      27                                                                                 ##STR41##                                                                         CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              168-170                                                                            mixture                                       28                                                                                 ##STR42##                                                                         CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              174-175                                                                            polar                                         29                                                                                 ##STR43##                                                                         CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              179-180                                                                            nonpolar                                      30  H    CH.sub.3 CHCl                                                                       CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              159-161                                                                            mixture                                       31  H    CH.sub.3 CHCl                                                                       CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              181-182                                                                            polar                                         32  H    CH.sub.3 CHCl                                                                       CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              185-186                                                                            nonpolar                                      33  H    CH.sub.3 CHCl                                                                       Cl   CH.sub.3 O                                                                         CH                                                                              169-170                                                                            mixture                                       34  H    CH.sub.3 CHCl                                                                       Cl   CH.sub.3 O                                                                         CH                                                                              174-175                                                                            polar                                         35  H    CH.sub.3 CHCl                                                                       Cl   CH.sub.3 O                                                                         CH                                                                              175-176                                                                            nonpolar                                      36  H    CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              176-178                                                                            mixture                                       37  H    CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              182-183                                                                            polar                                         38  H    CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              187-188                                                                            nonpolar                                      39  H    CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3 O                                                                         N 166-167                                                                            mixture                                       40  H    CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3 O                                                                         N 174-175                                                                            polar                                         41  H    CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3 O                                                                         N 179-180                                                                            nonpolar                                      42  H    CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              170-171                                                                            mixture                                       43  H    CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              173-174                                                                            polar                                         44  H    CH.sub.3 CHCl                                                                       CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              179-180                                                                            nonpolar                                      45                                                                                 ##STR44##                                                                         CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              153-154                                                                            mixture                                       46                                                                                 ##STR45##                                                                         CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              161-162                                                                            polar                                         47                                                                                 ##STR46##                                                                         CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              168-169                                                                            nonpolar                                      48                                                                                 ##STR47##                                                                         CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              151-152                                                                            mixture                                       49                                                                                 ##STR48##                                                                         CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              162-163                                                                            polar                                         50                                                                                 ##STR49##                                                                         CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              167-168                                                                            nonpolar                                      51                                                                                 ##STR50##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              138-139                                                                            mixture                                       52                                                                                 ##STR51##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              140-141                                                                            polar                                         53                                                                                 ##STR52##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              145-146                                                                            nonpolar                                      54                                                                                 ##STR53##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         Cl   CH                                                                              165-166                                                                            mixture                                       55                                                                                 ##STR54##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         Cl   CH                                                                              167-168                                                                            polar                                         56                                                                                 ##STR55##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         Cl   CH                                                                              171-172                                                                            nonpolar                                      57                                                                                 ##STR56##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3                                                                           N 154-156                                                                            mixture                                       58                                                                                 ##STR57##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3                                                                           N 169-170                                                                            polar                                         59                                                                                 ##STR58##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3                                                                           N 177-178                                                                            nonpolar                                      60  H    CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              152-153                                                                            mixture                                       61  H    CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              157-158                                                                            polar                                         62  H    CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              167-168                                                                            nonpolar                                      63  H    CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              140-142                                                                            mixture                                       64  H    CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              161-162                                                                            polar                                         65  H    CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              170-171                                                                            nonpolar                                      66  H    CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              152-154                                                                            mixture                                       67  H    CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              160-161                                                                            polar                                         68  H    CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              167-168                                                                            nonpolar                                      69  H    CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         Cl   CH                                                                              157-158                                                                            mixture                                       70  H    CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         Cl   CH                                                                              161-162                                                                            polar                                         71  H    CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         Cl   CH                                                                              171-172                                                                            nonpolar                                      72  H    CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3                                                                           N 141-142                                                                            mixture                                       73  H    CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3                                                                           N 167-168                                                                            polar                                         74  H    CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3                                                                           N 163-165                                                                            nonpolar                                      __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________     ##STR59##                                                                    Comp.                                                                         No. R    R.sup.1                                                                             X    Y    Z m.p. (°C.)                                                                  Remarks                                       __________________________________________________________________________    75                                                                                 ##STR60##                                                                         FCH.sub.2                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              144-146                                            76                                                                                 ##STR61##                                                                         FCH.sub.2                                                                           CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              139-141                                            77                                                                                 ##STR62##                                                                         FCH.sub.2                                                                           CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              130-132                                            78                                                                                 ##STR63##                                                                         FCH.sub.2                                                                           CH.sub.3 O                                                                         Cl   CH                                                                              138-139                                            79                                                                                 ##STR64##                                                                         FCH.sub.2                                                                           CH.sub.3 O                                                                         CH.sub.3                                                                           N 135-136                                            80                                                                                 ##STR65##                                                                         FCH.sub.2                                                                           CH.sub.3 O                                                                         CH.sub.3 O                                                                         N 129-131                                            81  H    FCH.sub.2                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              152-154                                            82  H    FCH.sub.2                                                                           CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              121-122                                            83  H    FCH.sub.2                                                                           CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              132-134                                            84  H    FCH.sub.2                                                                           CH.sub.3 O                                                                         Cl   CH                                                                              139-140                                            85  H    FCH.sub.2                                                                           CH.sub.3 O                                                                         CH.sub.3                                                                           N 141-142                                            86  H    FCH.sub.2                                                                           CH.sub.3 O                                                                         CH.sub.3 O                                                                         N 135-137                                            87                                                                                 ##STR66##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3                                                                           CH                                                                              155-157                                                                            mixture                                       88                                                                                 ##STR67##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3                                                                           CH                                                                              163-165                                                                            polar                                         89                                                                                 ##STR68##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3                                                                           CH                                                                              172-173                                                                            nonpolar                                      90                                                                                 ##STR69##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              135-136                                                                            mixture                                       91                                                                                 ##STR70##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              141-142                                                                            polar                                         92                                                                                 ##STR71##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              168-170                                                                            nonpolar                                      93                                                                                 ##STR72##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3                                                                           N 121-124                                                                            mixture                                       94                                                                                 ##STR73##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3                                                                           N 131-132                                                                            polar                                         95                                                                                 ##STR74##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3                                                                           N 142-143                                                                            nonpolar                                      __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________     ##STR75##                                                                    Comp.                                                                         No  R    R.sup.1                                                                             X    Y    Z m.p.(°C.)                                                                   Remarks                                       __________________________________________________________________________    96                                                                                 ##STR76##                                                                         CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              158-159                                                                            polar                                         97                                                                                 ##STR77##                                                                         CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              149-150                                                                            nonpolar                                      98                                                                                 ##STR78##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              138-139                                                                            polar                                         99                                                                                 ##STR79##                                                                         CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              131-134                                                                            nonpolar                                      100                                                                                ##STR80##                                                                         CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3 O                                                                         N 177-178                                                                            polar                                         101                                                                                ##STR81##                                                                         CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3 O                                                                         N      nonpolar                                      102 H    CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              178-179                                                                            polar                                         103 H    CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              161-162                                                                            nonpolar                                      104 H    CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              150-151                                                                            polar                                         105 H    CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3 O                                                                         CH                                                                              143-144                                                                            nonpolar                                      106 H    CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              183-184                                                                            polar                                         107 H    CH.sub.3 CHF                                                                        CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH                                                                              171-172                                                                            nonpolar                                      108 H    CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3 O                                                                         N 90-91                                                                              polar                                         109 H    CH.sub.3 CHF                                                                        CH.sub.3                                                                           CH.sub.3 O                                                                         N 99-100                                                                             nonpolar                                      110 H    CH.sub.2 F                                                                          CH.sub.3                                                                           Cl   CH                                                   111 H    CH.sub.2 F                                                                          CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              92-95                                              112 H    CH.sub.2 F                                                                          CH.sub.3                                                                           OCH.sub.3                                                                          CH                                                                              135-138                                            113 H    CH.sub.2 F                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                                                              139-141                                            114 H    CH.sub.2 F                                                                          OCH.sub.3                                                                          CH.sub.3                                                                           N 102-105                                            115                                                                                ##STR82##                                                                         CH.sub.2 F                                                                          CH.sub.3                                                                           Cl   CH                                                   116                                                                                ##STR83##                                                                         CH.sub.2 F                                                                          CH.sub.3                                                                           CH.sub.3                                                                           CH                                                                              178-179                                            117                                                                                ##STR84##                                                                         CH.sub.2 F                                                                          CH.sub.3                                                                           OCH.sub.3                                                                          CH                                                                              161-162                                            118                                                                                ##STR85##                                                                         CH.sub.2 F                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                                                              150-151                                            119                                                                                ##STR86##                                                                         CH.sub.2 F                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                          N 140-143                                            120                                                                                ##STR87##                                                                         CH.sub.3 CHF                                                                        CH.sub.3                                                                           OCH.sub.3                                                                          CH                                                                              157-158                                                                            mixture                                       123                                                                                ##STR88##                                                                         CH.sub.3 CHF                                                                        OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                                                              138-139                                                                            mixture                                       __________________________________________________________________________

Among the compounds of formula (I) as exemplified in the tables above,for example, a compound wherein R¹ is 1-flucroethyl can be present indifferent stereochemical isomeric forms because it has at least 2asymmetric carbon atoms in the substituent located at 3-position of thethienyl group. Therefore, these isomeric forms of the compound (I) arealso encompassed within the scope of the present invention. Thestereoisomeric racemates having polar and nonpolar forms can beseparated by known methods, e.g. column chromatography, thin layerchromatography, high performance liquid chromatography, into purestereoisomeric forms. In the present invention thin layer chromatographyor column chromatography on silica gel is selected. Since thesestereochemical configurations are early determined on the intermediateof formulae (I-4) to (I-6) and formula (II), the corresponding isomericform of formula (I) can be obtained by separating such intermediatesinto the desired stereochemical isomers which are then treated accordingto the process of the present invention.

the compound (I) of the present invention exhibits markedly highherbicidal activities either before or after emergence of weeds to becontrolled. Accordingly, the use of the compound of formula (I) as aherbicide for controlling weeds is also one object of the presentinvention.

Weeds herein, in the broadest sense, can be understood all plants whichgrow in locations where they are undesired.

3-(i-acetoxy-chloroethyl)-N- (4,6-dimethoxypyrimidin-2-yl)aminocarbonyl!-2-thiophenesulfonamide among the compound of formula (I)according to the present invention has an excellent herbicidal activity,particularly against Flatsedge and Arrowhead, as herbicide for waterconduit.

The amounts of the active compound (I) according to the presentinvention to be used can be determined depending on the kind of crops tobe protected or weeds to be controlled, and climate, weather,formulation, method of application, soil, and size of weeds. In general,the active compound is used in an amount of 0.01 to 10 kg per hectare,but can be used in an amount lower than the above defined amount whenthe soil to be treated has little organic matter or is a sandy soil.

For combating weeds, the active compound according to the presentinvention can be used alone or in a combination with known otherherbicides. Suitable herbicide which can be used in the combination withthe compound (I) according to the present invention can be examplifiedas follows:

    ______________________________________                                        Common Name                                                                   ______________________________________                                        acetochlor         acifluorfen                                                AC252, 214         AC263, 499                                                 acrolein           alachlor                                                   ametryn            amitrole                                                   AMS                asulam                                                     ASSURE             atrazine                                                   BAS-514            barban                                                     benefin            bensulfuron methyl                                         bensulide          bentazon                                                   benzolfluor        benzoylprop                                                bifenox            bromacil                                                   bromoxynil         butachlor                                                  buthidazole        butralin                                                   buthilate          cacodylic acid                                             CDAA               CDEC                                                       CGA 82725          CH-83                                                      chloramben         chlorbromuron                                              chlorimuron ethyl  chloroxuron                                                chlorporpham       chlorsulfuron                                              chlortoluron       cinmethylin                                                clethodim          clomazone                                                  cloproxydim        clopyralid                                                 CMA                cyanazine                                                  cycloate           cycluron                                                   cyperquat          cyprazine                                                  cyprazole          cypromid                                                   dalapon            dazomet                                                    DCPA               desmediphan                                                desmetryn          diallate                                                   dicamba            dichlorbenil                                               dichlorprop        dichlorfop                                                 diethatyl          difenzoquar                                                diphenmid          dipropetryn                                                diquat             diuron                                                     DNOC               DOWCO 453 ME                                               DPX-M6316          DSMA                                                       endothall          EPTC                                                       enthalfluralin     ethofumesate                                               EXPRESS            fenac                                                      fenoxapropethyl    fenuron                                                    fenuron TCA        flamprop                                                   fluazifop          fluazifopbutyl                                             fluometuron        fluorochloridone                                           fluorodifen        fluoroglycofen                                             fluridone          fomesafen                                                  fosamine           glyphosate                                                 haloxyfop          harmoney                                                   hexaflurate        hexazinone                                                 HW-52              imazamethabez                                              imazapyr           imazaquin                                                  imazthapyr         ioxynil                                                    isopropalin        isoproturon                                                isouron            isoxaben                                                   karbutilate        lactofen                                                   lenacil            linuron                                                    MAA                MAMA                                                       MCPA               MCPB                                                       mecoprop           mefluidide                                                 methalpropalin     methabenzthiazuron                                         metham             methazole                                                  methoxuron         metolachlor                                                metribuzin         metsulfuron methyl                                         MH                 milinate                                                   monolinuron        monuron                                                    monuron TCA        MSMA                                                       My-93              naproparmide                                               naproanilide       naptalam                                                   neburon            nitralin                                                   nitrofen           nitrofluorten                                              norea              norfrurazon                                                NTN-801            oryzalin                                                   oxadiazon          oxyfluorfen                                                paraquat           pebulate                                                   pendimethalin      perfluidone                                                phenmedipham       picloram                                                   PPG-1013           pretilachlor                                               procyazine         profluralin                                                prometon           prometryn                                                  pronamide          propachlor                                                 propanil           propazine                                                  propham            prosulfalin                                                prynachlor         pyrazon                                                    pyrazolate         quizalotop                                                 quizalotop ethyl   SC-2957                                                    secbumeton         sethoxydim                                                 siduron            simazine                                                   SL-49              sulfometuron methyl                                        TCA                tebuthiuron                                                terbacil           teruchlor                                                  terbuthyiazine     terbutol                                                   terbutryn          thiameruron methyl                                         thiobencarb        triallate                                                  riclopyr           tridiphane                                                 trifluralin        trimeturon                                                 2,4-D              2,4-DB                                                     vernolate          X-52                                                       xylachlor          Saturn                                                     KH-218             NSK-850                                                    Pyrazoxyfen        Dimension                                                  CH-900             Mefenacet                                                  TSH-888            Dymron                                                     Dimepiperate       Isoxapyrifos                                               Phenobenzuron      JC-940                                                     Esprocab           Methylbencab                                               Phenopylate        Benfuresate                                                S-275              Quinclorac                                                 Londax             NC-311                                                     TH-913             HW-52                                                      DEH-112            SKH-301                                                    Bromobutide        BAS517H                                                    RE45601            RE36299                                                    RO173664           HOE075632                                                  ICIA6051           DPXA7881                                                   MW801              CGA136872                                                  DPXV9360           DPXE9636                                                   SL950              ICIA02957                                                  CGAI42464          MY15                                                       MON7200            WL95481                                                    DPXY6202           MON15100                                                   SL160              ICIA0224                                                   LS83556            BAS518H                                                    CGA131036          DPXL5300                                                   HOE70542           ICIA0604                                                   ______________________________________                                    

The preparation and use of the active compound according to the presentinvention are more specifically explained by the following examples.However, it should be understood that they are provided only asrepresentative embodiment of the present invention and are not intendedto limit the scope of the present invention thereto.

EXAMPLE 1 Synthesis of N-t-butyl-3-(fluoroacetyl)-2-thiophenesulfonamide

2.98 g (0.0mole) of N-t-butyl-3-bromo-2-thiophenesulfonamide wasdissolved in 50mi of dry tetrahydrofuran and the mixture was cooled to-78° C. under nitrogen gas. To the reaction solution was slowly addeddropwise 8.4 ml of n-butyl lithium (2.5N) and then the temperature ofthe mixture was raised slowly to -20° C. and again cooled to -78° C. 1.2g (0.011 mole) of ethyl fluoroacetate was added slowly to the reactionmixture. The temperature of the mixture was raised again slowly to -20°C. and then the mixture was stirred for 10 minutes. To the reactionmixture was added 100 ml of 5% aqueous ammonium chloride solution, andthen added 100 ml of ethylacetate to separate the organic layer. Theextracted organic layer was dried over anhydrous magnesium sulfate andconcentrated. The residue was subjeced to column chromatography onsilica gel to obtain 2.0 g (Yield: 72%) of the pure title compound as aliquid.

¹ H NMR(CDCl₃, δ): 1.25(s, 9H), 5.4(d, 2H), 6.1(s, 1H), 7.3-7.6 (m, 2H)

EXAMPLE 2 Synthesis ofN-t-butyl-3-(1-acetoxy-2-fluoroethyl)-2-thiophenesulfonamide

1.4 g (0.005 mole) of N-t-butyl-3-(fluoroacetyl)-2-thiophenesulfonamidesynthesized in Example 1 was dissolved in 100 ml of methanol and then190 mg (0.005 mole) of sodium borohydride (NaBH₄) was added slowlythereto. The mixture was stirred at 40° C. for 30 minutes and thenconcentrated under reduced pressure. The residue was dissolved in 30 mlof methylene chloride and the resulting solution was washed with 5%aqueous hydrochloric acid solution. To the solution were added aceticanhydride, pyridine and N,N-dimethyl amidepyridine, and the mixture wasstirred at normal temperature for 24 hours and then washed with 5%aqueous hydrochloric acid solution. The organic layer was separated,dried over anhydrous magnesium sulfate and filtered. The filtrate Wasconcentrated and the residue was subjected to column chromatography onsilica gel to obtain 1.4 g (Yield: 85% of the title compound.

¹ H NMR(CDCl₃, δ): 1.23(s, 9H), 2.13(s, 3H), 4.65(dd, 2H), 5.7(s, 1H),6.55 (dt, 1H), 7.2 (dd, 1H), 7.5(d, 1H)

EXAMPLE 3 Synthesis of3-(1-acetoxy-2-fluoroethyl)-2-thiophenesulfonamide

1.4 g (0.0043 mole) of N-t-butyl-3-(1-aceoxy-2-fluoroethyl)-2-thiophenesulfonamide synthesized in Example 2 dissolved in 5 ml oftrifluoroacetic acid. The reaction solution was stirred at normaltemperature for 12 hours and then concentrated under reduced pressure.The residue was dissolved in methylene chloride and washed with aqueoussodium bicarbonate solution. The organic layer was separated, dried overanhydrous magnesium sulfate and then filtered. The filtrate wasconcentrated. The residue was recrystallized to obtain 750 mg (Yield:74%) of the pure title compound as a white solid.

m.p. : 94°-96° C. ¹ H NMR(CDCl₃, δ): 2.13(s, 3H), 4.55(dd, 2H), 5.7(s,2H), 6.55(dt, 1H), 7.2(dd, 1H), 7.53(d, 1H)

EXAMPLE 4 Synthesis of N-(4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl!-3-(1-acetoxy-2-fluoroethyl)-2-thiophenesulfonamide(Compound No. 1)

667 mg (0.0025 mole) of3-(1-acetoxy-2-fluoroethyl)-2-thiophenesulfonamide synthesized inExample 3 and 687 mg (0.0025 mole) ofN-(4,6-dimethoxy-2-pyrimidinyl)-O-phenylcarbamate were dissolved in 10ml of dry acetonitrile. To the reaction solution was added 400 mg ofDBU, and the mixture was stirred at normal temperature for 4 hours andthen concentrated. The residue was dissolved in 90 ml of methylenechloride, and the resulting solution as washed with 5% aqueous HClsolution. The organic layer was separated, dried and then concentrated.The residue was recrystallized to obtain 835 mg (Yield: 78%) of the puretitle compound as a while solid.

m.p. : 131°-134° C. ¹ H NmR(CDCl₃, δ): 2.13(s, 3H), 4.01(s, 6H),4.48-4.97(m, 2H), 5.85(s, 1H), 6.61-6.78(m, 1H), 7.24 (br, 1H),7.2-7.75(m, 2H), 13.1(s, 1H)

EXAMPLE 5 Synthesis of N-(4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl!-3-(1-hydroxy-2-fluoroethyl)-2-thiophenesulfonamide(Compound No. 4)

650 mg (0.0015 mole) of N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl!-3-(1-acetoxy-2-fluoroethyl)-2-thiophenesulfonamidesynthesized in Example 4 was dissolved in 5 ml of aqueous sodiumhydroxide solution and then stirred at normal temperature for one hour.The reaction mixture was adjusted to pH4 by adding 5% aqueous HClsolution and then extracted with methylene chloride. The extract wasconcentrated to obtain 540 mg (Yield: 92%) of the pure title compound.

m.p. : 135°-136° C. ¹ H NMR(CDCl₃, δ): 4.01(s, 6H), 4.41-4.88(m, 2H),5.85 (s, 1H), 5.91-6.08(m, 1H), 7.55(s, 1H), 7.3-7.7(m, 2H), 13.0(s, 1H)

EXAMPLE 6 Synthesis of N-t-butyl-3-chloroacetyl-2-thiophenesulfonamide

2.98 g (0.0| mole) of N-t-butyl-3-bromo-2-thiophenesulfonamide wasdissolved in 50 ml of dry tetrahydrofura mixture was cooled to -78° C.under nitrogen gas. To the reaction solution was slowly added dropwise8.4 ml of n-butyl lithium(2.5N) and then the temperature of the mixturewas raised slowly to -20° C. and again cooled to -78° C. 1.4 g (0.012mole) of ethyl chloroacetates was added slowly to the mixture. Thetemperature of the reaction mixture was raised slowly to -20° C. againand then the mixture was stirred for 10 minutes. To the mixture wasadded 100 ml of aqueous ammonium chloride solution and then added 100 mlof ethyl acetate to separate the organic layer. The extracted organiclayer was dried over anhydrous magnesium sulfate and then concentrated.The residue was subjected to column chromatography on silica gel toobtain 1.9 g (Yield: 69%) of the pure title compound as a liquid.

¹ H NMR(CDCl₃, δ): 1.25(s, 9H), 4.7(s, 2H), 6.7(s, 1H), 7.52 (d, 1H),7.57 (d, 1H)

EXAMPLE 7 Synthesis ofN-t-butyl-3-(1-acetoxy-2-chloroethyl)-2-thiophenesulfonamide

1.5 g (0.005 mole) of N-t-butyl-3-(chloroacetyl)-2-thiophenesulfonamidesynthesized in Example 6 was dissolved in the combined solution of 1 mlof acetic acid and 10 ml of tetrahydrofuran and then 0.31 g (0.005 mole)of sodium cyanoborohydride was added slowly thereto. The reactionsolution was stirred at normal temperature for 30 minutes and thensubjected to a vacuum evaporator to remove the solvent. To the residuewas added 10 ml of water and then the resulting solution was extractedwith methylene chloride. The extract was dried over anhydrous magnesiumsulfate and filtered. To the filtrate were added acetic anhydride,pyridine and N,N-dimethylaminopyridine and the mixture was stirred atnormal temperature for 24 hours and then washed with 5% aqueoushydrochloric acid solution. The organic layer was separated, dried overanhydrous magnesium sulfate and filtered. The filtrate was concentratedand the residue was subjected to column chromatography on silica gel toobtain 5 g (Yield: 84%) of the title compound. ¹ H NMR(CDCl₃, δ): 1.3(s,9H), 2.15(s, 3H), 3.57-3.9(m, 2H), 5.23(s, 1H), 6.5(m, 1H), 7.13(d, 1H),7.5 (d, 1H)

EXAMPLE 8 Synthesis of3-(1-acetoxy-2-chloroethyl)-2-thiophenesulfonamide

1.5 g (0.0044 mole) ofN-t-butyl-3-(1-acetoxy-2-chloroethyl)-2-thiophenesulfonamide synthesizedin Example 7 was dissolved in 5 ml of trifluoroacetic acid. The reactionsolution was stirred at normal temperature for 12 hours and thenconcentrated under reduced pressure. The residue was dissolved inmethylene chloride and the solution was washed with aqueous sodiumbicarbanate solution. The organic layer was separated, dried overanhydrous magnesium sulfate and filtered. The filtrate was thenconcentrated. The residue was subjected to column chromatograpy onsilica gel to obtain 760 mg (Yield: 72%) of the pure title compound.

m.p. : 90°-91° C. ¹ H NMR(CDCl₃, δ): 2.1(s, 3H), 3.75-3.85(m, 2H),5.55(s, 1H), 6.5(m, 1H), 7.5(d, 1H), 7.52(d, 1H)

EXAMPLE 9 Synthesis of N-(4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl!-3-(1-acetoxy-2-chloroethyl)-2-thiophenesulfonamide(Compound No. 7)

709 mg (0.0025 mole) of3-(1-acetoxy-2-chloroethyl)-2-thiophenesulfonamide synthesized inExample 8 and 687 mg (0.0025 mole) ofN-(4,6-dimethoxy-2-pyrimidinyl)-O-phenylcarbamate were treated accordingto the same procedure as Example 4 to obtain 750 mg (Yield: 70%) of thepure title compound.

m.p.: 150°-151° C. ¹ H NMR(CDCl₃, δ): 2.02(s, 3H), 3.81-3.98(m, 2H),4.0(s, 6H), 5.8(s, 1H), 6.61(m, 1H), 7.21-7.67 (m, 2H), 7.3(s, 1H),13.18(s, 1H)

EXAMPLE 10 Synthesis ofN-t-butyl-2-(fluoroacetyl)-3-thiophenesulfonamide

1.87 g (0.01 mole) of N-t-butyl-3-thiophenesulfonamide was treatedaccording to the same procedure as Example 1 to obtain 2.1 g (Yield:76%) of the pure title compound as a liquid.

¹ H NMR(CDCl₃, δ): 1.25(s, 9H), 5.4(d, 2H), 6.1(s, 1H), 7.3-7.6 (m, 2H)

EXAMPLE 11 Synthesis ofN-t-butyl-2(1-acetoxy-2-fluoroethyl)-3-thiophenesulfonamide

1.4 g (0.005 mole) of N-t-butyl-2-(fluoroacetyl)-3-thiophenesulfonamidesynthesized in Example 10 was treated according to the same procedure asExample 2 to obtain 1.5 g (Yield: 91%) of the title compound.

¹ H NMR(CDCl₃, δ): 1.23(s, 9H), 2.13(s, 3H), 4.45-4.88 (m, 2H), 5.2 (s,1H), 6.82 (dt, 1H), 7.25-7.4 (m, 2H)

EXAMPLE 12 Synthesis of2-(1-acetoxy-2-fluoroethyl)-3-thiophenesulfonamide

1.4 g (0.0043 mole) ofN-t-butyl-2-(1-acetoxy-2-fluoro-ethyl)-3-thiophenesulfonamidesynthesized in Example 11 was treated according to the same procedure asExample 3 to obtain 750 mg (Yield.: 74%) of the pure title compound as awhite solid.

m.p.: 97°-98° C. ¹ H NMR(CDCl₃, δ): 2.13(s, 3H), 4.67(dd, 2H), 5.58(s,2H), 6.52(dt, 1H), 7.2(dd, 1H),7.55(d, 1H)

EXAMPLE 13 Synthesis of N-(4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl!-2-(1-acetoxy-2-fluoroethyl)-3-thiophenesulfonamide(Compound No. 77)

667 mg (0.0025 mole) of2-(1-acetoxy-2-fluoroethyl)-3-thiophenesulfonamide synthesized inExample 12 and 687 mg (0.0025 mole) ofN-(4,6-dimethoxy-2-pyrimidinyl)-O-phenyl-carbamate were treatedaccording to the same procedure as Example 4 to obtain 780 mg (Yield:73%) of the pure title compound as a white solid.

m.p. : 130°-132° C.

¹ H NMR(CDCl₃, δ): 2.19(s, 3H), 4.01(s, 6H), 4.6-5.0(m, 2H), 5.81(s,1H), 6.98-7.0(m,1H), 7.3(s, 1H), 7.38-7.6(d, 2H), 12.82(s, 1H)

EXAMPLE 14 Synthesis of N-(4r6-dimethoxypyrimidin-2-yl)-aminocarbonyl!-2-(1-hydroxy-2-fluoroethyl)-3-thiophenesulfonamide(Compound No. 83)

650 mg (0.0015 mole) of N-(4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl!-2-(1-acetoxy-2-fluoroethyl)-3-thiophenesulfonamidesynthesized in Example 13 was treated a the same procedure as Example 5to obtain 528 mg (Yield: 90%) of the pure title compound.

m.p. : 132°-134° C.

¹ H NHR(CDCl₃, δ): 4.0(s, 6H), 4.6-5.0(m, 2H), 5.81(s, 1H), 5.91-6.08(m,1H), 7.55(s, 1H), 7.3-7.7 (m, 2H), 13.0(s, 1H)

EXAMPLE 15 Synthesis ofN-t-butyl-4-(2-fluoropropionyl)-3-thiophenesulfonamide

2.98 g (0.01 mole) of N-t-butyl-4-bromo-3-thiophene sulfonamide wasdissolved in 50 ml of dry tetrahydrofuran and the mixture was cooled to-78° C. under nitrogen gas. To the reaction solution was slowly addeddropwise 8.4 ml of n-bury lithium (2.5N) and then the temperature of themixture was raised slowly to -20° C. and again cooled to -78° C. 1.32 g(0.011 mole) of ethyl fluoropropionyl was added slowly to the reactionmixture. The temperature of the mixture was raised slowly to -20° C.again and then the mixture was stirred for 10 minutes. To the mixturewas added 100 ml of 5% aqueous ammonium chloride solution and then added100 ml of ethylacetate to separate the organic layer. The extractedorganic layer was dried over anhydrous magnesium sulfate andconcentrated. The residue was subjected to column chromatography onsilica gel to obtain 1.77 g (Yield: 68%) of the pure title compound as aliquid.

¹ H NMR(CDCl₃, δ): 1.23(s, 9H), 1.65(dd, 3H), 5.45(dt, 2H),

6.18(s, 1H), 7.65-7.75(m, 2H)

EXAMPLE 16 Synthesis of polor and nonpolarN-t-butyl-4-(1-acetoxy-2-fluropropyl)-3-thiophenesulfonamide

2.6 g (0.01 mole) of N-t-butyl-4-(fluropropionyl)-3-thiophenesulfonamidewas dissolved in 100 ml of methanol and then 380 mg (0.01 mole) ofsodium borohydride was added slowly thereto. The reaction solution wasstirred at 40° C. for 30 minutes and then concentrated under reducedpressure. The residue was dissolved in 30 ml of methylene chloride andwashed with 5% aqueous hydrochloric acid solution. To the solution wereadded acetic anhydride, pyridine and N,N-dimethylamido pyridine and themixture was stirred at normal temperature for 24 hours and then washedwith 5% aqueous hydrochloric acid solution. The organic layer wasseparated, dried over anhydrous magnesium sulfate and filtered. Thefiltrate was concentrated and the residue was identified as a mixture oferythro and threo diastereomers by thin layer chromatography. Theisomers were separated by column chromatography on silica gel to obtainthe polar and nonpolar title compound.

polar compound: 1.2 g (Yield: 86%) ¹ H NMR(CDCl₃, δ); 1.25(s, 9H),1.31(dt, 3H), 2.1(s, 3H), 4.8(s, 1H), 4.8-5.2(m, 1H), 6.25(dd, 1H),7.2-7.4(m, 2H)

nonpolar compound: 1.1 g (Yield: 78%) ¹ H NMR(CDCl₃, δ); 1.25(s, 9H),1.32(dt, 3H), 2.1(s, 3H), 4.8(s, 1H), 4.8-5.3(m, ¹ H), 6.15(dd, 1H),7.2-7.4(m, 2H)

EXAMPLE 17 Synthesis of4-(1-acetoxy-2-fluoropropyl)-3-thiophenesulfonamide (polar)

1.4 g (0.0043 mole) ofN-t-butyl-4-(1-acetoxy-2-fluoropropyl)-3-thiophenesulfonamide (polar)synthesized in Example 16 was treated according to the same procedure asExample 3 to obtain 750 mg (Yield: 74%) of the pure title compound as awhite solid.

m.p.: 92°-94° C. ¹ H NMR(CDCl₃, δ): 1.25(dt, 3H), 2.1(s, 3H), 4.85-5.25(m, 1H), 5.55(s, 2H), 6.35(dd, 1H), 7.1-7.2(m, 2H)

EXAMPLE 18 Synthesis of4-(1-acetoxy-2-fluoropropyl)-3-thiomphenesulfonamide(nonpolar)

1.4 g (0.0043 mole) of N-t-butyl-4-(1-acetoxy-2-fluoropropyl)propyl)-3-thiophenesulfonamide (nonpolar) synthesized in Example 16 wastreated according to the same procedure as Example 3 to obtain 750 mg(Yield: 74%) of the pure title compound as a which solid.

m.p. : 91°-93° C.

¹ H NMR(CDCl₃, δ): 1.32(dt, 3H), 2.1(s, 3H), 4.6-5.1(m, 1H), 5.65(s,2H), 6.28(dd, 1H), 7.1-7.2(m, 2H)

EXAMPLE 19 Synthesis of N- (4.6-dimethoxypyrimidin-2-yl)aminocarbonyl!-4-(1-acetoxy-2-fluoropropyl)-3-thiophenesulfonamide(molar) (Compound No. 98)

670 mg (0.0025 mole) of4-(1-acetoxy-2-fluoropropyl)-3-thiophenesulfonamide (polar) synthesizedin Example 17 and 687 mg (0.0025 mole) ofN-(4,6-dimethoxy-2-pyrimidinyl)-O-phenylcarbamate were treated accordingto the same procedure as Example 4 to obtain 853 mg (Yield: 78%) of thepure title compound as a white solid.

m.p. : 138°-139° C.

¹ H NMR(CDCl₃, δ): 1.5(m, 3H), 4.01(s, 6H), 5.0(m, 1H), 6.0(dd, 1H),6.78(s, 1H), 7.3-7.4(m, 2H), 9.2(s, 1H), 13.1(s, 1H)

EXAMPLE 20 Synthesis of N- (4,6-dimethoxypyrimidin-2-yl)aminocarbonyl-4-(1-acetoxy-2-fluoropropyl)-3-thiophenesulfonamide(nonpolar)(CompoundNo. 99.)

670 mg (0.0025 mole) of4-(1-acetoxy-2-fluoropropyl)-3-thiophenesulfonamide (nonpolar)synthesized in Example 18 and 687 mg (0.0025 mole) ofN-(4.6-dimethoxypyrimidin-2-pyrimidinyl)-O-phenylcarbamate were treatedaccording to the same procedure as Example 4 to obtain 820 mg (Yield:75%) of the pure title compound as a white solid.

m.p.: 131°-134° C.

¹ H NMR(CDCl₃, δ): 1.4(dt, 3H), 3.95(s, 6H), 4.9-5.3(m, 1H), 5.8(s, 1H),6.0-6.2(m, 1H), 7.3(m, 2H), 7.8(s, 1H), 12.7(s, 1H)

The herbicidal effect of the compound according to the present inventionwas identified by experiments in greenhouse as described hereinafter.

EXAMPLE 21 Pre-emergence treatment test

To produce a suitable preparation, 1 part by weight of active compoundwas mixed with 5 parts by weight of acetone and 1 part by weight ofalkylarylpolyglycolether as emulsifier and then solubilized. Theresulting solution was diluted with water to the desired concentration.

Seeds of the test plants were sown in normal soil and, after 24 hours,the preparation containing the active compound as prepared above wasapplied. It is expedient to keep constant the amount of water per unitarea. In addition, the concentration of the active compound in thepreparation is very important. After three weeks, the degree of damageof the plants was rated in % damage in comparison to the development ofthe untreated control, and the evaluation result was represented asfollows:

0%=no action (like untreated control)

20%=trivial effect

70%=herbicidal effect

100%=total destruction (complete withering to death)

EXAMPLE 22 Post-emergence treatment test

A preparation containing the active compound was produced according tothe same procedure as Example 21. Test plants which have a height of 5to 15 cm were sprayed with the above preparation in such a way as toapply the desired amount of the active compound per unit area. Theconcentration of the active ingredient in solution for spraying wasdetermined in such a way that the desired amount of the active compoundcan be applied when 2000 L of water was sprayed per hectare. After threeweeks, the degree of damage of the plants was rated in % damage incomparison to the development of the untreated control, and theevaluation result was represented as in Example 21.

As a result of test, it could be identified that the compound of formula(I) according to the present invention has an excellent herbicidalactivity on monocotyledon or dicotyledon weeds by both pre- andpost-emergence treatment.

EXAMPLE 23 Paddy Submerged Test

A small amount of fertilizer was added to a round pot(60 cm or 140 cm)and then the pot was filled with sterilized paddy field soil in pastestate up to 5 cm in depth. Seeds of Barnyard grass, Umbrella plant, DayFlower, Mono-choria, Toothcup, Ludwigia, Bulrush, False pimpernel, andperennial bulbs such as Flat-sedge, Arrowhead were mixed or sown in asurface layer of the soil and then seedlings (at the stage of 2 to 3leaves) of the rice plant were planted in a depth of 2 cm from thesurface at a population of one root per pot. After transplantation, theywere submerged in fresh water at a depth of 2 cm and keeped in such astate for one day. Then, they were uniformly treated by applyingdropwise the preparation which was prepared as in Example 21 (4 mg perpot when the applied amount of the preparation is 4 kg/ha). After twoweeks, the herbicidal activity was evaluated and the result wasrepresented according to the same criteria as in Example 21.

In the present invention, the herbicidal activities of the activecompounds used in the pre- and post-emergence treatment tests accordingto Examples 21 and 22 are represented in the following Tables 4, 5 and6.

                                      TABLE 4                                     __________________________________________________________________________    TEST FOR DETERMINATION OF EFFECTIVE CON-                                      CENTRATION(HERBICIDE)-Water in paddy field                                            Appl.                                                                 Camp.                                                                             Appl.                                                                             Conc.                                                                 No. Time                                                                              (kg/ha)                                                                           A   B  C   D  E   F  G                                            __________________________________________________________________________    1   2   .05 95  100                                                                              100 100                                                                              100 100                                                                              100                                                  .0125                                                                             95  95 100 90 100 100                                                                              100                                                  .00312                                                                            60  90 75  90 95  100                                                                              95                                           4   2   .05 95  100                                                                              100 100                                                                              100 100                                                                              100                                                  .0125                                                                             95  95 95  90 100 100                                                                              100                                          7   2   .05 90  100                                                                              100 100                                                                              100 100                                                                              100                                                  .0125                                                                             80  100                                                                              90  90 100 100                                                                              100                                                  .00312                                                                            30  60 0   90 85  100                                                                              100                                                  .00078                                                                            0   0  0   80 30  95 90                                           8   2   .05 95  100                                                                              100 100                                                                              100 100                                                                              100                                                  .0125                                                                             80  90 90  100                                                                              100 100                                                                              100                                                  .00312                                                                            20  70 40  90 80  70 90                                                   .00078                                                                            0   0  0   90 0   0  90                                           30  2   .05 80  100                                                                              100 100                                                                              100 100                                                                              100                                                  .0125                                                                             50  80 100 100                                                                              80  100                                                                              80                                           31  2   .05 80  100                                                                              100 100                                                                              100 100                                                                              100                                                  .0125                                                                             60  80 95  100                                                                              90  100                                                                              100                                                  .00312                                                                            20  60 70  100                                                                              95  100                                                                              100                                          32  2   .05 50  80 100 100                                                                              90  100                                                                              100                                                  .0125                                                                             0   40 50  90 60  90 90                                           43  2   .05 95  100                                                                              100 100                                                                              100 100                                                                              100                                                  .0125                                                                             50  70 100 100                                                                              80  85 90                                           44  2   .05 40  70 100 100                                                                              90  80 100                                                  .0125                                                                             0   20 30  90 60  40 90                                           48  2   .05 50  100                                                                              100 100                                                                              100 90 100                                                  .0125                                                                             20  50 60  100                                                                              60  30 90                                           49  2   .05 80  100                                                                              100 100                                                                              100 100                                                                              100                                                  .0125                                                                             40  50 100 100                                                                              100 60 100                                          50  2   .05 50  100                                                                              100 100                                                                              100 89 100                                                  .0125                                                                             10  30 60  90 100 30 100                                          51  2   .05 70  90 100 100                                                                              100 100                                                                              100                                                  .0125                                                                             30  40 70  100                                                                              100 100                                                                              100                                          52  2   .05 70  100                                                                              100 100                                                                              100 100                                                                              100                                                  .0125                                                                             50  90 100 100                                                                              100 100                                                                              100                                                  .00312                                                                            0   30 30  90 90  100                                                                              100                                          53  2   .05 65  100                                                                              100 100                                                                              100 100                                                                              100                                                  .0125                                                                             20  40 90  100                                                                              100 100                                                                              100                                                  .00312                                                                            0   0  0   40 100 70 100                                          76  2   .05 80  90 100 100                                                                              100 100                                                                              100                                                  .0125                                                                             30  50 10  90 80  50 90                                           77  2   .05 70  100                                                                              90  100                                                                              100 100                                                                              100                                                  .0125                                                                             30  80 10  90 90  80 90                                           82  2   .5  100 100                                                                              100 100                                                                              100 100                                                                              100                                                  .125                                                                              90  100                                                                              100 100                                                                              100 100                                                                              100                                                  .03125                                                                            80  90 100 100                                                                              100 100                                                                              100                                                  .00781                                                                            60  80 100 90 100 90 100                                          112 2   .05 70  70 70  90 90  100                                                                              100                                                  .1  100 100                                                                              100 100                                                                              100    90                                                   .025                                                                              80  70 50  80 80     60                                           113 2   .05 90  100                                                                              80  100                                                                              100 100                                                                              100                                              1   .1  100 100                                                                              100 100                                                                              100    100                                                  .025                                                                              100 90 90  100                                                                              100    100                                          120 2   .05 60  60 90  70     90 80                                                   .05 40  70 90  90 80  70 80                                           98  2   .05 40  40 50  40 90  100                                                                              90                                                   .05 30  60 70  90 90  50 90                                           99  2   .05 75  100                                                                              100 100                                                                              100 100                                                                              100                                                  .0125                                                                             40  60 50  90 60  80 80                                           __________________________________________________________________________     Note:                                                                         1) Application Time 1 = preemergence                                          2 = postemergence                                                             2) A: Rice plant (at the stage of 3 leaves)                                   B: Rice plant                                                                 C: Barnyard grass                                                             D: Bulrush                                                                    E: Monochoria                                                                 F: Flatsedge                                                                  G: Arrowhead                                                             

                                      TABLE 5                                     __________________________________________________________________________    TEST ON HERBICIDAL EFFECT                                                                Appl.                                                              Comp.                                                                             Application                                                                          Conc.                                                              No. Time   (kg/ha)                                                                           H  C  I J  K  L  M N O  P                                      __________________________________________________________________________    2   pre-emergence                                                                        .05 80 100                                                                              25                                                                              85 85 60 30                                                                              65                                                                              70 90                                         post-emergence                                                                       .05 60 90 15                                                                              55 75 20 15                                                                              40                                                                              40 70                                     3   pre-emergence                                                                        .05 65 60 0 25 60 15 0 0 0                                             post-emergence                                                                       .05 50 60 10                                                                              0  10 15 0 0 0  25                                     5   pre-emergence                                                                        .05 85 100                                                                              15                                                                              100                                                                              100                                                                              50 20                                                                              65                                                                              75 95                                         post-emergence                                                                       .05 65 100                                                                              15                                                                              55 100                                                                              20 15                                                                              25                                                                              30 90                                     6   pre-emergence                                                                        .05 60 40 0 45 70 45 0 0 0  0                                          post-emergence                                                                       .05 30 60 0 0  0  10 0 0 0  0                                      35  pre-emergence                                                                        .05 100                                                                              90 0 40 60 60 0 40                                                                              60 100                                        post-emergence                                                                       .05 70 80 0 40 50 60 40                                                                              0 100                                                                              100                                    57  pre-emergence                                                                        .05 85 30 0 20 15 0  0 0 0  15                                         post-emergence                                                                       .05 65 10 0 0  0  15 0 0 30 15                                     58  pre-emergence                                                                        .05 90 60 10                                                                              60 60 10 0 10                                                                              65 65                                         post-emergence                                                                       .05 65 50 10                                                                              0  15 0  0 0 20 60                                     75  pre-emergence                                                                        .05 60 100                                                                              40                                                                              50 70 30 20                                                                              0 80 90                                         post-emergence                                                                       .05 60 40 20                                                                              0  60 80 0 0 90 60                                     76  pre-emergence                                                                        .05 100                                                                              100                                                                              80                                                                              100                                                                              100                                                                              70 70                                                                              70                                                                              100                                                                              100                                        post-emergence                                                                       .05 70 100                                                                              60                                                                              50 100                                                                              40 60                                                                              20                                                                              100                                                                              80                                     77  pre-emergence                                                                        .05 90 100                                                                              60                                                                              100                                                                              90 50 40                                                                              90                                                                              90 100                                        post-emergence                                                                       .05 90 100                                                                              60                                                                              60 100                                                                              60 70                                                                              60                                                                              100                                                                              90                                     81  pre-emergence                                                                        .05 100                                                                              100                                                                              80                                                                              100                                                                              100                                                                              80 60                                                                              60                                                                              90 90                                         post-emergence                                                                       .05 60 100                                                                              40                                                                              40 100                                                                              100                                                                              40                                                                              0 70 100                                    120 pre-emergence                                                                        .05 100                                                                              100                                                                              0 50 70 40 40                                                                              60                                                                              80 100                                        post-emergence                                                                       .05 70 80 0 50 20 0  40                                                                              0 90 80                                     96  pre-emergence                                                                        .05 70 70 0 100                                                                              60 60 50                                                                              50                                                                              80 90                                         post-emergence                                                                       .05 70 50 0 30 20 20 0 0 80 60                                     97  pre-emergence                                                                        .05 80 90 60                                                                              100                                                                              100                                                                              80 60                                                                              70                                                                              90 100                                        post-emergence                                                                       .05 80 50 0 20 70 0  0 0 60 50                                     123 pre-emergence                                                                        .05 60 80 0 100                                                                              90 70 0 50                                                                              80 100                                        post-emergence                                                                       .05 80 50 0 20 80 50 0 0 80 70                                     98  pre-emergence                                                                        .05 30 30 0 60 60 60 0 0 80 100                                        post-emergence                                                                       .05 70 50 0 0  60 30 30                                                                              0 70 50                                     99  pre-emergence                                                                        .05 90 70 0 100                                                                              90 70 70                                                                              70                                                                              80 100                                        post-emergence                                                                       .05 80 70 0 0  70 30 40                                                                              60                                                                              80 50                                     __________________________________________________________________________     Note:                                                                         H: Sorghum                                                                    C: Barnyard grass                                                             I: Quackgrass                                                                 J: Larger carbgrass                                                           K: American panicum                                                           L: Black nightshade                                                           M: Indian Joint vetch                                                         N: Abutilon avicennae                                                         0: Cocklebur                                                                  P: Bindweed                                                              

                                      TABLE 6                                     __________________________________________________________________________    TEST ON HERBICIDAL EFFECT                                                            Appl.                                                                  Comp.                                                                             Appl.                                                                            Conc.                                                                  No. Time                                                                             (kg/ha)                                                                           Q  R  S  T  U  H  C  I  J  K  L  M  N  O  P                        __________________________________________________________________________    1   pre-                                                                             .1  100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                          emer                                                                             .025                                                                              100                                                                              100                                                                              100                                                                              60 100                                                                              100                                                                              100                                                                              80 100                                                                              100                                                                              90 80 90 100                                                                              100                          gence                                                                            .006                                                                              40 70 90 30 100                                                                              100                                                                              100                                                                              50 100                                                                              100                                                                              90 60 80 90 100                          post-                                                                            .1  100                                                                              100                                                                              80 70 100                                                                              100                                                                              100                                                                              80 60 100                                                                              80 100                                                                              100                                                                              100                                                                              100                          emer                                                                             .025                                                                              60 100                                                                              50 30 90 100                                                                              100                                                                              70 40 100                                                                              70 60 100                                                                              100                                                                              100                          gence                                                                            .006                                                                              0  100                                                                              20 0  30 90 90 50 0  100                                                                              20 20 60 70 50                       4   pre-                                                                             .1  100                                                                              100                                                                              100                                                                              80 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                          emer                                                                             .025                                                                              100                                                                              90 90 30 100                                                                              100                                                                              100                                                                              70 100                                                                              100                                                                              100                                                                              60 100                                                                              100                                                                              100                          gence                                                                            .006                                                                              100                                                                              70 80 20 100                                                                              100                                                                              100                                                                              60 100                                                                              100                                                                              90 60 80 90 100                          post-                                                                            .1  100                                                                              100                                                                              80 60 100                                                                              100                                                                              100                                                                              70 60 100                                                                              60 100                                                                              100                                                                              100                                                                              100                          emer                                                                             .025                                                                              90 100                                                                              60 40 80 100                                                                              100                                                                              70 30 100                                                                              50 60 100                                                                              100                                                                              100                          gence                                                                            .006                                                                              0  90 30 20 40 70 60 40 0  100                                                                              0  0  60 70 70                       7   pre-                                                                             .1  60 80 90 40 100                                                                              100                                                                              100                                                                              40 100                                                                              100                                                                              70 60 80 100                                                                              100                          emer                                                                             .025                                                                              50 70 80 20 100                                                                              90 100                                                                              30 80 100                                                                              60 50 70 100                                                                              90                           gence                                                                            .00625                                                                            0  50 70 0  70 60 80 0  50 100                                                                              40 30 60 90 90                           post-                                                                            .1  60 100                                                                              60 40 80 100                                                                              100                                                                              80 65 100                                                                              70 80 70 100                                                                              100                          emer                                                                             .025                                                                              50 90 30 30 70 90 100                                                                              30 40 100                                                                              60 70 60 80 90                           gence                                                                            .00625                                                                            40 70 0  0  50 50 70 0  0  50 30 30 40 70 50                       8   pre-                                                                             .1  100                                                                              100                                                                              90 90 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              80 90 80 100                                                                              100                          emer                                                                             .025                                                                              70 80 80 60 100                                                                              100                                                                              100                                                                              60 100                                                                              100                                                                              60 50 70 100                                                                              100                          gence                                                                            .00625                                                                            60 60 60 20 90 80 100                                                                              30 80 90 50 40 60 90 100                          post-                                                                            .1  100                                                                              100                                                                              100                                                                              60 100                                                                              100                                                                              100                                                                              80 100                                                                              100                                                                              30 80 70 100                                                                              100                          emer                                                                             .025                                                                              70 100                                                                              50 40 80 60 100                                                                              40 40 90 0  40 50 90 100                          gence                                                                            .00625                                                                            0  60 30 0  60 40 70 0  30 20 0  0  0  70 80                       26  pre-                                                                             .1  100                                                                              90 90 100                                                                              100                                                                              90 100                                                                              90 100                                                                              90 70 60 60 100                                                                              100                          emer                                                                             .025                                                                              70 70 80 50 100                                                                              80 100                                                                              70 90 80 60 40 0  80 100                          gence                                                                            .00625                                                                            50 30 0  0  80 70 100                                                                              40 50 70 40 20 0  70 100                          post-                                                                            .1  60 100                                                                              70 60 100                                                                              50 100                                                                              40 40 70 0  50 0  80 40                           emer                                                                             .025                                                                              20 100                                                                              30 40 70 40 90 20 30 40 0  30 0  60 0                            gence                                                                            .00625                                                                            0  50 0  0  20 0  30 0  20 30 0  0  0  0  0                        32  pre-                                                                             . 1 90 70 100                                                                              0  100                                                                              100                                                                              100                                                                              40 100                                                                              90 60 80 70 90 100                          emer                                                                             .025                                                                              60 50 100                                                                              0  100                                                                              90 100                                                                              30 60 90 60 60 60 80 100                          gence                                                                            .00625                                                                            50 40 50 0  80 40 65 0  30 60 40 20 20 80 100                          post-                                                                            .1  90 100                                                                              50 0  50 70 100                                                                              40 40 80 40 90 40 100                                                                              80                           emer                                                                             .025                                                                              70 100                                                                              20 0  30 50 90 0  20 70 30 80 30 100                                                                              40                           gence                                                                            .00625                                                                            20 70 0  0  0  40 30 0  0  40 0  40 0  70 20                       44  pre-                                                                             1   100                                                                              90 80 20 100                                                                              100                                                                              100                                                                              60 100                                                                              90 65 70 70 100                                                                              100                          emer                                                                             .025                                                                              100                                                                              50 70 0  90 90 100                                                                              30 100                                                                              90 50 40 40 100                                                                              100                          gence                                                                            .00625                                                                            30 30 60 0  65 60 80 0  60 50 30 0  20 100                                                                              100                          post-                                                                            .1  100                                                                              100                                                                              70 0  40 80 100                                                                              40 50 80 30 70 40 100                                                                              100                          emer                                                                             .025                                                                              70 70 60 0  20 30 80 0  40 70 20 40 30 90 80                           gence                                                                            .00625                                                                            20 40 30 0  0  0  70 0  20 30 0  20 0  80 30                       47  pre-                                                                             .2  100                                                                              90 90 40 100                                                                              100                                                                              100                                                                              50 100                                                                              100                                                                              60 70 100                                                                              100                                                                              100                          emer                                                                             .05 100                                                                              70 80 30 100                                                                              100                                                                              100                                                                              30 100                                                                              100                                                                              40 30 100                                                                              100                                                                              100                          gence                                                                            .0125                                                                             40 60 60 0  60 60 100                                                                              0  100                                                                              90 20 0  50 100                                                                              100                          post-                                                                            .2  100                                                                              80 90 50 60 100                                                                              100                                                                              40 100                                                                              100                                                                              60 100                                                                              100                                                                              100                                                                              100                          emer                                                                             05  80 70 70 0  40 100                                                                              100                                                                              0  50 70 40 50 80 90 100                          gence                                                                            .0125                                                                             0  30 40 0  0  30 60 0  0  40 0  0  40 70 40                       48  pre-                                                                             .2  100                                                                              100                                                                              100                                                                              80 100                                                                              100                                                                              100                                                                              80 100                                                                              100                                                                              100                                                                              90 100                                                                              100                                                                              100                          emer                                                                             .05 100                                                                              80 100                                                                              50 100                                                                              100                                                                              100                                                                              60 100                                                                              100                                                                              90 80 80 100                                                                              100                          gence                                                                            .0125                                                                             80 70 60 0  100                                                                              90 100                                                                              40 100                                                                              90 80 50 80 100                                                                              100                          post-                                                                            .2  100                                                                              100                                                                              100                                                                              60 100                                                                              100                                                                              100                                                                              65 100                                                                              100                                                                              60 100                                                                              90 100                                                                              100                          emer                                                                             05  90 100                                                                              90 50 100                                                                              90 100                                                                              60 60 90 50 100                                                                              80 100                                                                              100                          gence                                                                            .0125                                                                             60 80 80 30 70 60 80 40 30 80 20 80 60 100                                                                              100                      49  pre-                                                                             .2  100                                                                              90 90 60 100                                                                              100                                                                              100                                                                              70 100                                                                              100                                                                              60 90 100                                                                              100                                                                              100                          emer                                                                             .05 100                                                                              70 90 40 100                                                                              100                                                                              100                                                                              60 100                                                                              90 50 65 70 100                                                                              100                          gence                                                                            .0125                                                                             60 50 70 0  80 80 100                                                                              40 90 50 40 40 20 90 100                          post-                                                                            .2  100                                                                              100                                                                              90 50 70 100                                                                              100                                                                              60 100                                                                              100                                                                              60 70 100                                                                              100                                                                              90                           emer                                                                             .05 100                                                                              90 70 30 60 100                                                                              100                                                                              30 50 100                                                                              40 60 60 100                                                                              80                           gence                                                                            .0125                                                                             40 40 60 0  40 60 60 0  0  40 0  0  20 80 40                       51  pre-                                                                             .2  100                                                                              100                                                                              100                                                                              40 100                                                                              100                                                                              100                                                                              70 100                                                                              100                                                                              90 80 90 100                                                                              100                          emer                                                                             .05 90 90 100                                                                              30 100                                                                              100                                                                              100                                                                              40 100                                                                              100                                                                              80 70 80 90 90                           gence                                                                            .0125                                                                             65 65 60 0  90 90 100                                                                              0  70 100                                                                              70 40 60 90 90                           post-                                                                            .2  100                                                                              100                                                                              60 50 100                                                                              100                                                                              100                                                                              70 70 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                          emer                                                                             .05 90 100                                                                              50 20 90 100                                                                              100                                                                              50 50 100                                                                              50 100                                                                              90 100                                                                              100                          gence                                                                            .0125                                                                             80 100                                                                              30 0  50 70 90 0  30 100                                                                              20 50 50 90 90                       52  pre-                                                                             .2  100                                                                              100                                                                              100                                                                              60 100                                                                              100                                                                              100                                                                              60 100                                                                              100                                                                              90 100                                                                              100                                                                              100                                                                              100                          emer                                                                             .05 90 90 100                                                                              40 100                                                                              100                                                                              100                                                                              40 100                                                                              100                                                                              80 70 90 100                                                                              100                          gence                                                                            .0125                                                                             80 60 90 10 100                                                                              90 100                                                                              0  90 100                                                                              50 60 70 100                                                                              100                          post-                                                                            .2  100                                                                              100                                                                              90 60 100                                                                              100                                                                              100                                                                              80 90 100                                                                              70 100                                                                              90 100                                                                              100                          emer                                                                             .05 100                                                                              100                                                                              60 40 80 100                                                                              100                                                                              70 70 100                                                                              50 100                                                                              70 100                                                                              100                          gence                                                                            .0125                                                                             60 90 40 0  50 90 100                                                                              20 40 90 40 90 40 100                                                                              100                      53  pre-                                                                             .2  100                                                                              70 60 20 100                                                                              100                                                                              100                                                                              20 100                                                                              100                                                                              60 60 100                                                                              100                                                                              100                          emer                                                                             .05 60 60 40 0  100                                                                              90 100                                                                              0  70 100                                                                              50 20 70 100                                                                              100                          gence                                                                         post-                                                                            .2  100                                                                              100                                                                              60 20 50 100                                                                              100                                                                              30 60 100                                                                              60 100                                                                              100                                                                              100                                                                              100                          emer                                                                             .05 80 100                                                                              30 0  30 100                                                                              100                                                                              0  30 80 30 60 100                                                                              90 60                           gence                                                                     64  pre-                                                                             .1  100                                                                              90 90 70 100                                                                              100                                                                              100                                                                              80 100                                                                              100                                                                              70 90 100                                                                              100                                                                              100                          emer                                                                             .025                                                                              100                                                                              80 80 40 100                                                                              100                                                                              100                                                                              60 100                                                                              100                                                                              50 60 80 100                                                                              100                          gence                                                                            .00625                                                                            70 50 60 40 90 90 100                                                                              50 100                                                                              100                                                                              30 20 30 100                                                                              100                          post-                                                                            .1  100                                                                              100                                                                              90 60 100                                                                              100                                                                              100                                                                              60 100                                                                              100                                                                              50 100                                                                              100                                                                              100                                                                              100                          emer                                                                             .025                                                                              100                                                                              70 80 30 90 90 100                                                                              20 50 80 20 80 50 100                                                                              100                          gence                                                                            .00625                                                                            50 60 60 0  60 40 70 0  20 20 0  30 20 100                                                                              40                       66  pre-                                                                             .1  100                                                                              100                                                                              90 30 100                                                                              100                                                                              100                                                                              60 100                                                                              100                                                                              70 80 80 100                                                                              100                          emer                                                                             .025                                                                              80 60 80 20 100                                                                              90 100                                                                              40 100                                                                              100                                                                              60 30 70 100                                                                              100                          gence                                                                            .00625                                                                            30 30 20 0  60 50 90 20 80 100                                                                              50 0  40 100                                                                              100                          post-                                                                            .1  100                                                                              100                                                                              70 40 100                                                                              100                                                                              100                                                                              40 100                                                                              100                                                                              70 100                                                                              100                                                                              100                                                                              100                          emer                                                                             .025                                                                              70 90 50 20 90 70 100                                                                              20 40 90 70 60 70 100                                                                              100                          gence                                                                            .00625                                                                            0  70 20 0  50 60 60 0  0  60 20 20 40 80 40                       67  pre-                                                                             .1  100                                                                              90 80 40 100                                                                              100                                                                              100                                                                              70 100                                                                              100                                                                              70 90 90 100                                                                              100                          emer                                                                             .625                                                                              100                                                                              80 70 20 100                                                                              100                                                                              100                                                                              50 100                                                                              90 60 60 80 100                                                                              100                          gence                                                                            .00625                                                                            40 50 30 0  90 80 100                                                                              0  80 80 50 40 30 90 100                          post-                                                                            .1  100                                                                              100                                                                              70 40 100                                                                              100                                                                              100                                                                              40 100                                                                              100                                                                              80 100                                                                              100                                                                              100                                                                              100                          emer                                                                             .025                                                                              90 100                                                                              60 20 100                                                                              100                                                                              100                                                                              20 50 100                                                                              50 70 80 100                                                                              60                           gence                                                                            .00625                                                                            60 60 40 0  65 80 90 0  30 100                                                                              30 40 40 100                                                                              40                       82  pre-                                                                             .1  100                                                                              90 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              70 80 80 100                                                                              100                          emer                                                                             .025                                                                              100                                                                              70 90 60 100                                                                              100                                                                              100                                                                              80 100                                                                              100                                                                              60 60 30 80 100                          gence                                                                            .00625                                                                            60 30 40 20 100                                                                              70 100                                                                              40 60 90 30 0  0  50 100                          post-                                                                            .1  100                                                                              100                                                                              80 60 90 70 100                                                                              60 70 80 30 80 40 100                                                                              100                          emer                                                                             .025                                                                              50 100                                                                              60 20 80 40 80 40 30 70 20 40 0  90 60                           gence                                                                            .00625                                                                            20 60 30 0  60 0  50 0  0  40 0  0  0  30 20                       111 pre-                                                                             .1  70 60 40 70 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              70 20 0  100                                                                              100                          emer                                                                             .05 60 20 0  60 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              60 0  0  50 100                          gence                                                                         post-                                                                            .1  100                                                                              50 20 20 100                                                                              100                                                                              100                                                                              50 100                                                                              100   40 20 80 100                          emer                                                                             .05 40 40 0  0  100                                                                              80 100                                                                              40 80 100   20 0  65 100                          gence                                                                     112 pre-                                                                             .1  100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              70 100                                                                              100                                                                              100                                                                              100                          emer                                                                             .05 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              50 100                                                                              100                                                                              100                                                                              100                          gence                                                                            .025                                                                              100                                                                              100                                                                              100                                                                              65 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              40 70 80 100                                                                              100                          post-                                                                            .1  100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100   100                                                                              100                                                                              100                                                                              100                          emer                                                                             .05 100                                                                              100                                                                              100                                                                              65 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100   100                                                                              100                                                                              100                                                                              100                          gence                                                                            .025                                                                              100                                                                              100                                                                              90 30 100                                                                              90 100                                                                              100                                                                              100                                                                              100   80 40 90 60                       113 pre-                                                                             .1  100                                                                              100                                                                              100                                                                              60 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              50 100                                                                              100                                                                              100                                                                              100                          emer                                                                             .05 100                                                                              100                                                                              100                                                                              40 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              40 100                                                                              100                                                                              100                                                                              100                          gence                                                                            .025                                                                              90 100                                                                              70 20 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              30 50 100                                                                              100                                                                              100                          post-                                                                            .1  100                                                                              100                                                                              70 60 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100   100                                                                              100                                                                              100                                                                              100                          emer                                                                             .05 100                                                                              100                                                                              60 40 100                                                                              100                                                                              100                                                                              90 100                                                                              100   100                                                                              100                                                                              100                                                                              100                          gence                                                                            .025                                                                              100                                                                              100                                                                              60 0  100                                                                              100                                                                              100                                                                              80 70 100   100                                                                              100                                                                              100                                                                              90                       __________________________________________________________________________     Note:                                                                         Q: Corn                                                                       R: Bean                                                                       S: Cotton                                                                     T: Wheat                                                                      U: Rice plant                                                                 H: Sorghum                                                                    C: Barnyard grass                                                             I: Quackgrass                                                                 J: Larger carbgrass                                                           K: American panicum                                                           L: Black nightshade                                                           M: Indian joint vetch                                                         N: Abutilon avicennae-                                                        0: Cocklebur                                                                  P: Bindweed                                                              

What is claimed is:
 1. A thiophenesulfonylurea derivative represented bythe following general formula (I): ##STR89## and a salt thereof, inwhich T represents a group T1, T2, or T3 having the following generalformula: ##STR90## wherein E represents a direct bond;R representshydrogen or C₁₋₄ acyl; R¹ represents C₁₋₆ alkyl substituted with 1 to 3halogen atoms; R² represents hydrogen, C₁₋₃ alkyl, C₁₋₃ haloalkyl,halogen, cyano, C₁₋₃ alkoxy, C₁₋₃ haloalkoxy, amino, methylamino,dimethylamino, or C₁₋₂ alkyl substituted with C₁₋₂ alkoxy, C₁₋₂haloalkoxy, thiol, methylthio, cyano or hydroxy; A represents a groupselected from the group consisting of A1 to A4 having the followingformulae: ##STR91## wherein X represents hydrogen, C₁₋₄ alkyl, C₁₋₄alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, C₁₋₄ alkylthio, C₁₋₄haloalkylthio, halogen, C₂₋₅ alkoxyalkyl, C₂₋₅ alkoxyalkoxy, imino, C₁₋₃alkylamino, di(C₁₋₃ alkyl)amino or C₃₋₅ cycloalkyl; X¹ represents C₁₋₂alkyl, C₁₋₂ alkoxy or C₁₋₂ alkylthio; Y represents hydrogen, C₁₋₄ alkyl,C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₁₋₄ haloalkylthio, C₁₋₄ alkylthio, C₂₋₅alkoxyalkyl, C₂₋₅ alkoxyalkoxy, amino, C₁₋₃ alkylamino, di(C₁₋₃alkyl)amino, C₃₋₄ alkenyloxy, C₃₋₄ alkynyloxy, C₂₋₅ alkylthioalkyl, C₁₋₄haloalkyl, C₂₋₄ alkynyl, azido, cyano, C₂₋₅ alkylsulfinylalkyl, C₂₋₅alkylsulfonylalkyl, hydroxymethyl, C₃₋₅ cycloalkyl or C₃₋₅ cycloalkoxy;Y¹ represents oxygen or methylene; Y² represents hydrogen or methyl; andZ represents N or CH;provided that (1) when X is fluoro, chloro, iodo, Zrepresents CH and Y represents methoxy, ethoxy, methoxymethylamino,amino, methylamino, dimethylamino or difluoromethoxy and (2) when X or Yis difluoromethoxy, Z represents CH and (3) when the total number ofcarbon atoms of X and Y is 4 or more, R² represents a group having up to4 carbon atoms.
 2. The compound of formula (I) according to claim 1,wherein T represents T1, T2, or T3 wherein R represents hydrogen oracetyl, R¹ represents methyl or ethyl substituted with halogen and R²represents hydrogen; and A represents A1 wherein X and Y eachindependently represent C₁₋₄ alkyl, C₁₋₄ alkoxy or halogen and Zrepresents N or CH.
 3. The compound of formula (I) according to claim 1,wherein T represents T1 wherein R represents hydrogen or acetyl, R¹represents methyl or ethyl substituted with fluorine or chlorine and R²represents hydrogen; and A represents A1 wherein X and Y eachindependently represents methyl, methoxy or chloro and Z represents N orCH.
 4. The compound of formula (I) according to claim 1, which is N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl!-3-(1-acetoxy-2-fluoroethyl)-2-thiophenesulfonamide.5. The compound of formula (I) according to claim 1, which is N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl!-3-(1-acetoxy-2-chloroethyl)-2-thiophenesulfonamide.6. The compound of formula (I) according to claim 1, which is N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl!-3-(1-acetoxy-2-chloropropyl)-2-thiophenesulfonamide.7. The compound of formula (I) according to claim 1, which is N-4,6-dimethoxypyrimidin-2-yl)aminocarbonyl!-3-(2-fluoro-1-hydroxyethyl)-2-thiophenesulfonamide.8. The compound of formula (I) according to claim 1, which is N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl!-3-(1-acetoxy-2-fluropropyl)-2-thiophenesulfonamide.9. The compound 3-(1-acetoxy-2-fluoroethyl)-2-thiophenesulfonamide. 10.The compound 3-(1-acetoxy-2-chloroethyl)-2-thiophenesulfonamide.
 11. Thecompound 3-(1-acetoxy-2-fluoropropyl)-2-thiophenesulfonamide.
 12. Aherbicidal composition which contains the compound of formula (I)defined in claim 1 as an active ingredient.
 13. The herbicidalcomposition according to claim 12, which contains the compound offormula (I) wherein T represents T1 wherein R represents hydrogen oracetyl, R¹ represents ethyl or propyl substituted with halogen; and Arepresents A1, as an active ingredient.
 14. The herbicidal compositionaccording to claim 12, which contains the compound of formula (I) whichis N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl!-3-(1-acetoxy-2-chloroethyl)-2-thiophenesulfonamideas an active ingredient.
 15. The herbicidal composition according toclaim 12, which contains the compound of formula (I) which is N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl!-3-(1-acetoxy-2-fluoropropyl)-2-thiophenesulfonamide as anactive ingredient.